Today you’re getting two for the price of one (…still free). Roxy Te Owens was one of the very first friends I made through blogging. We met when I was still in college and she was just leaving her first job and trying to figure out her next steps. Fast forward five years and she’s at the helm of Society Social, a line of furniture that she designs and that’s been featured in every blog and magazine ever. She’s found her footing, moved to New York, carved out a niche for herself, and brought back the bar cart in her spare time. I’m continually blown away by her can do attitude and so proud to call her one of my friends.

Roxy introduced me to Inslee Farriss, an insanely talented artist with whom she shares a chic-as-can-be office space in SoHo. She does custom illustrations for gifts and wedding, sells prints and stationery on her website, and also writes the most clever blog you’ll ever read. They’re two of the most brilliant, charming, and innovative women I’ve met and I know you’ll all love getting to know more about them!

What was your first job ever? Have you always wanted to do what you’re doing now?Inslee: My first job was in a clothing boutique when I was 18. I’ve always wanted to be in the fashion/design/art arena, but I didn’t always know this would be my career. For a long time, I thought that illustration was just an outlet for me to be creative, an escape from a “normal” job. It took me a while to realize that my creative outlet could be my source of income.Roxy: Yes! Mine was at a retail store at the local mall when I was 16. I didn’t know it then but my experience helped me land amazing internships while I was at Parsons. The fashion brands I worked for liked that I already had experience on the sales floor dealing with customers and in-store merchandising. Never underestimate a modest first job!

When did you know it was time to launch your business?Roxy: It was more of a gradual realization versus one moment. I was in my third year of a corporate job in the buying office of a large department store. I was buying for about 300 stores and helping manage millions of dollars. Not only was it extremely stressful but it was also the same drill every day: 9 to 5 (though usually 7 or 8) in a gray cubicle hammering away at a computer. It wasn’t rewarding or fulfilling — not the kind of life I wanted to live!Inslee: I didn’t really realize it until after I’d started my business… Whoops! I launched my website and sold a small collection of stationery while I was still in school. It was very much a back-burner side project. For a long time, my parents fielded the requests that were coming into my website while I was finishing up my degree at Washington & Lee. After graduation, we transitioned into me reading and replying to those emails directly. When I realized how many people were interested in my illustrations and willing to pay for them, I quit my post-graduate unpaid internship and threw myself fully into growing my art into a brand.

Tell me a little about the process of creating a new piece.Roxy: My designs start with a variety of things: a look I love, a fabric, or a proper cocktail hour! I’m not technically trained so my team of designers and engineers are instrumental in making my ideas come to life. For my first bar carts, I knew I wanted to incorporate lots of faux bamboo, fretwork, natural cane, color, and functionality. There’s a lot of dialogue and brainstorming around the key attributes of my initial ideas, then sketches, then editing, then the spec’ing of the product. The designs that make the cut go to prototyping and on to production. It’s a fun collaboration with all parties involved but nothing makes it to the next stage without my direct approval.Inslee: When I’m working on something like my yearly calendar or a new card design, I create a big secret Pinterest board and compile tons of image inspiration. When I’m working for a client, I let their vision inform how I work. I always ask what little details make them unique. Things like “I always wear these earrings my grandmother gave me” or “please make me five inches taller” are common remarks that help me capture my subjects.

What does a typical day look like for you?Roxy: Running a small business requires you to take charge of many roles, from designer to bookkeeper to marketing manager, so every day is different. I’m always learning something new!Inslee: The beauty of this job is that there rarely is a typical day. Today began with working on a new blog post and then I had a client come in to meet with me about a commission… the subject of which is “two little girls and their cat, Olaf!” This afternoon I’ll be working on an interesting mix of administrative and creative work: both installing our air-conditioning unit and beginning a new bridal commission.

You crack me up. Besides your new AC unit, what’s inspiring you right now?Inslee: I just launched a new product that I’m so inspired to work on: large, gestural nudes done in bright watercolor washes and sumi ink. It’s so much fun for me to do something different from my usual pen and ink and watercolor small character sketches.Roxy: Travel! I just returned from a spectacular Mediterranean cruise. We visited Italy, Greece, and Croatia. The buildings were powder blue, bright pink, salmon, terracotta, minty green, golden yellow, and so much more. And the sea! Deep, saturated shades of cerulean and teal. I want to splash my apartment and all of Society Social with the hues of the Mediterranean!

That sounds amazing! What’s the most fun part of your job?

Roxy: It is my absolute favorite to receive notes and pictures from my sweet customers. It’s still surreal to think these designs started out as just a thought, and seeing them in real homes – styled by real people – gets me every time. My customers’ enthusiasm keeps me going!

Inslee: I love interacting with my clients. It is by far the most fun part. I love helping them celebrate important milestones with commissions, launch new businesses with illustrations for their websites and branding, and plan parties with illustrations for invitation designs.

And the least fun, just to keep it real?

Inslee: Trying to find more than 24 hours in each and every day. Being an independent and creative entrepreneur is a major undertaking and requires a ton of focus, energy, and the ability to wear many hats. You try installing an AC unit and painting a bridal portrait in the same 2 hour window and tell me how it goes [laughing].

Roxy: The least fun is the uncertainty of it all. I’m relatively new at this so there are definitely days when I feel overwhelmed and unsure of myself.

I know that feeling all too well. How do you stay organized?

Inslee: I use Salesforce to keep trace of my incoming leads and commissions. I would be lost without it.

Roxy: Google Calendar! I wouldn’t know what day it is without it.

I need to start using both of those! What’s one goal you have for your business in the next year or two?

Roxy: At this point most of my wholesale business has come through my website, but I would love to see how buyers would respond to SS at an industry trade show. I can’t decide between the NYC show, the Atlanta show, and High Point, of course. Any feedback would be greatly appreciated!

Inslee: I’d love to establish myself as a resource for not just illustration work but fine art (like my nudes) and other larger pieces.

What’s one pinch me moment you’ve had so far?Roxy: About three years ago, I was unemployed and deeply entrenched in the 20-something battle of finding my life path and passion. Sounds dramatic, right? Well, it was! When I see my designs in national glossies, I still can’t believe it. I’m so grateful.Inslee: Well, I can’t reveal too much just yet, but I’m partnering with an NYC stationer with a rich history in the finest of papers. Our collaboration will launch in a matter of weeks so stay tuned!

That’s so exciting! When will you know you’ve made it?Inslee: When we can afford an apartment with a dishwasher.Roxy: Really all I’m asking for is a little more natural light and a second bedroom. 😉You know you live in New York when… Ha! Any advice for the next generation of creative entrepreneurs?Roxy: Five tips, to be exact!Inslee: Learn how to build and code your own websites!!!

This is my favorite so far of your career spotlights!! Inslee’s illustrations are just amazing… I can’t wait to find out about her new project! They are inspirations. Now I need to get me a bar cart and a commissioned illustration (both things on my list to get!!)

These are two of my favorite brands and business ladies! This is such a great article. I love all of their products, especially how unique they are and how custom-made they feel (ie, not cookie cutter). So excited to keep following their careers! They both seem fantastic and are clearly so creative. Maybe in the future they will open a brick and mortar store together…I would be first in line to shop!

I adore following these two on social and I am such a fan of their work! What an inspiring post. I just thought to myself last night, “I’ll know I’m at a successful point in my career when I can afford an NYC apartment with a dishwasher and laundry that’s at least in the building,” so their answers completely resonate with me, ha!

I didn’t get a chance to comment on your feedback post so here it is: I love the Career Spotlights! Keep them coming 🙂 It’s always inspiring to hear that it’s possible to work for yourself in a creative way (as I type this from my desk in a 7000-person company.)

Inslee did a commission for me for my boyfriend’s sister’s wedding, and it stole the show! She absolutely loved it!